N-Sulfinylpyrrolidine-containing ureas and thioureas as bifunctional organocatalysts

• Viera Poláčková,
• Dominika Krištofíková,
• Boglárka Némethová,
• Renata Górová,
• Mária Mečiarová and
• Radovan Šebesta

Beilstein J. Org. Chem. 2021, 17, 2629–2641, doi:10.3762/bjoc.17.176

• pre-catalysts (S,R)-5a and (S,S)-5a A stirred solution of (R)-tert-butanesulfinamide or (S)-tert-butanesulfinamide (0.09 g, 0.75 mmol) in THF (5 mL) was cooled to 0 °C under argon atmosphere. Butyllithium in hexane (0.35 g, 0.82 mmol) was added dropwise, and the solution was stirred for 15 min. The

• )-tert-butanesulfinamide (0.07 g, 0.6 mmol) in THF (5 mL) was cooled to −30 °C under argon atmosphere. Butyllithium in hexane (0.28 g, 0.66 mmol) was added dropwise and the solution was stirred for 15 min. The solution of (S)-tert-butyl 2-(isocyanatomethyl)pyrrolidine-1-carboxylate (3b, 0.15 g, 0.66 mmol

• , 2973, 1653, 1159, 1237, 1058 cm−1; HRMS (m/z): [M + Na]+ calcd for C15H29N3O3S2, 386.1543; found, 386.1543; [M + H]+ calcd, 364.1729; found, 364.1722. General procedure for the preparation of N-sulfinylurea pre-catalysts (S,R)-5b and ((S,S)-5b) A stirred solution of (R)-tert-butanesulfinamide or (S

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

• Joseane A. Mendes,
• Paulo R. R. Costa,
• Miguel Yus,
• Francisco Foubelo and
• Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

A novel and practical asymmetric synthesis of dapoxetine hydrochloride

• Yijun Zhu,
• Zhenren Liu,
• Hongyan Li,
• Deyong Ye and
• Weicheng Zhou

Beilstein J. Org. Chem. 2015, 11, 2641–2645, doi:10.3762/bjoc.11.283

• ., Shanghai 201203, China 10.3762/bjoc.11.283 Abstract A novel and practical asymmetric synthesis of dapoxetine hydrochloride by using the chiral auxiliary (S)-tert-butanesulfinamide was explored. The synthesis was concise, mild, and easy to perform. The overall yield and stereoselectivity were excellent

• . Keywords: asymmetric synthesis; dapoxetine hydrochloride; stereoselectivity; (S)-tert-butanesulfinamide; Introduction Premature ejaculation (PE) is the most frequent form of ejaculatory dysfunction with a distribution of 39% of the general male population [1][2]. Dapoxetine hydrochloride (1, (S)-(+)-N,N

• route for the synthesis of (S)-dapoxetine (1) through this chiral auxiliary. Results and Discussion Herein, a novel and practical synthesis of 1 (Scheme 1) based on (S)-tert-butanesulfinamide (2) was developed. 3-(Naphthalen-1-yloxy)-1-phenylpropan-1-one (3), which was commercially available from J&K